Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilizers

ABSTRACT

The present invention relates to the use of an amino compound, which is an esteramine or an amidoamine surfactant with improved biodegradability, as an adjuvant for agrochemically active compounds such as pesticides or fertilizers. The adjuvant has Formula (I) where R1 is an aliphatic group containing 7-22 carbon atoms; EO is an ethyleneoxy group; Y is 0 or NH; R2 and R3 is independently CH 2 CH 2 OH or an alkyl group with 1-5 carbon atoms, preferably 1-3 carbon atoms; n is a number between 0-10; x is a number 0-1 provided that when Y is O, then x is 1, and when Y is NH, then x is O; and m is a number 2-6, preferably 2-3, provided that when Y is NH, then m is 3-6, preferably 3; or an adduct obtained by reacting one mole of the compound with 1-5 moles of an alkylene oxide having 2-3 carbon atoms. The esteramines are obtained from an ethoxylated alcohol that has been carboxymethylated and then esterified with a tertiary hydroxyamine (alkanolamine), and the amidoamines are obtained by reaction between a fatty acid or a fatty acid methyl ester and a diamine, such as N,N-bishydroxyethyl-1,3-propylenediamine.

The present application was filed on May 25, 2001 as internationalapplication serial number PCT/SE01/01178 and claims priority of Swedishpatent application No. 0002230-1 filed on Jun. 15, 2000.

The present invention relates to the use of an amino compound, which isan esteramine or an amidoamine surfactant with improvedbiodegradability, as an adjuvant for agrochemically active compoundssuch as pesticides or fertilizers. The esteramines are obtained from anethoxylated alcohol that has been carboxymethylated and then esterifiedwith a tertiary hydroxyamine (alkanolamine), and the amidoamines areobtained by reaction between a fatty acid or a fatty acid methyl esterand a diamine, such as N,N-bishydroxyethyl-1,3-propylenediamine.

It is well known that the uptake as well as the efficacy of manypesticides and fertilizers can be improved by the addition of so calledadjuvants. A variety of surfactants have been used for this purpose, andmany of them are nitrogen containing. The surfactant group that has beenmost widely used in this connection is the fatty amine ethoxylates, butalso other types of compounds have been described as adjuvants forpesticides or fertilizers. In EP-A1-0 638 236 is described anagricultural chemical composition containing as an adjuvant compounds ofthe esteramine type mentioned above. The esteramines disclosed in thatpublication all referred to compounds having two fatty alkyl chains. InWO 97/05779 plant protection compositions containing water-solubleactive materials and one or more polyethoxylated amidoamines containingtwo carbon atoms between the amido and amino groups were claimed.

However, nowadays there is an increasing demand in most areas forcompounds that are readily biodegradable. This is also the case withinthe agrochemical field, where adjuvants with a better biodegradabilitycombined with a good ability to improve the uptake and efficacy ofpesticides and fertilizers are being sought for. Thus, the purpose ofthe present invention is to provide adjuvants for pesticide formulationsand for formulations containing fertilizers that are at least aseffective as the prior used amino compounds. Another purpose is toprovide adjuvants with an improved biodegradability compared to priorknown amino compounds used as adjuvants.

It has now been found that compounds with the formula (I)

where R1 is an aliphatic group containing 7-22 carbon atoms; EO is anethyleneoxy group; Y is O or NH; R2 and R3 is independently —CH₂CH₂OH,—CH₂CH(CH₃)OH or an alkyl group with 1-5 carbon atoms, preferably 1-3carbon atoms; n is a number between 0-10; x is a number 0 or 1 providedthat when Y is O, then x is 1, and when Y is NH, then x is 0; and m is anumber 2-6, preferably 2-3, provided that when Y is NH, then m is 3-6,preferably 3; or an adduct obtained by reacting one mole of the compoundwith 1-5 moles of an alkylene oxide having 2-3 carbon atoms; can be usedas adjuvants in agrochemical compositions. When reacting the compound offormula I and an alkylene oxide having 2-3 carbon atoms, the alkyleneoxide will be added to the groups containing active hydrogen atoms,and/or will be inserted into the ester or amide groups by rearrangementreactions. The compounds of the invention are readily biodegradable andare very effective in improving the efficacy of pesticides andfertilizers. Another benefit of the compounds is that they do not showany, or very little, eye irritancy. Some of the compounds can beformulated together with a pesticide or fertilizer, giving clearsolutions of low viscosity, whereas others give solutions that are ofmoderate viscosity or turbid. These latter solutions often separategradually into two phases. It has been found that also in these casesstable low-viscous solutions can be obtained by the addition of an alkylglycoside according to the formula ROG_(p), where R is an alkyl groupcontaining 6-10 carbon atoms, preferably 6-8, G is a monosaccharideresidue and p is a number between 1-5. Surprisingly it has been foundthat the addition of an alkyl glycoside, besides giving rise to clear,stable solutions of low viscosity, also enhances the effect of theadjuvants of the invention. The alkyl glycosides are also readilybiodegradable, so there is no disadvantage in adding them to theformulations.

Suitable examples of compounds according to the present invention arethe esteramines described by the formula (II)

where R4 is an alkyl group containing 8-22, preferably 8-18, carbonatoms, n is 2-7, m is a number 2-3 and R2 and R3 is independently—CH₂CH₂OH, —CH₂CH(CH₃)OH or an alkyl group with 1-5, preferably 1-3carbon atoms. N,N-Dimethylethanolamine esters of this type have beendescribed in e.g. U.S. Pat. No. 4,228,042, where they were used asintermediates to produce quaternary surfactants for use in laundrydetergent compositions.

Other suitable examples of compounds according to the present inventionare the amidoamines described by the formula (III):

where R5 is an alkyl group containing 7-21, preferably 7-17, carbonatoms. Such amidoamines have been described in EP-A2-0 265 824, wherethey were used as intermediates for zwitterionic phosphate estersurfactants for use in personal care, and also in DT-A1-2641286, wherethey were used as intermediates for quaternary ammonium compounds foruse as impregnating agents for cellulose fibre materials.

In formulations containing an active amount of the amino compounds as anadjuvant, the amount of amino compound can vary within wide limits, butis normally from 5% to 500% by weight calculated on the amount ofpesticide or fertilizer present in the formulation, preferably between10% to 200%, and most preferably between 15% to 80%.

The product (II) may easily be produced by reacting an ethercarboxylicacid according to formula (IV),

where R4 and n have the meaning mentioned above for formula II, with analkanolamine such as N-methyldiethanolamine, triethanolamine,3-dimethylamino-1-propanol or N,N-dimethylethanolamine. Suitableexamples of hydrophobic groups R4 in formula IV are 2-ethylhexyl, octyl,decyl, coco alkyl, lauryl, oleyl, rapeseed alkyl and tallow alkyl.

The product (III) may easily be produced by reacting a fatty acid, orthe methyl ester of a fatty acid, withN,N-bishydroxyethyl-1,3-propylenediamine. Suitable fatty acids are2-ethylhexanoic acid, octanoic acid, decanoic acid, coco fatty acid,lauric acid, rapeseed fatty acid, oleic acid and tallow fatty acid. Theproduct based on coco fatty acid is most preferred.

Suitable processes for the production of the amidoamine compounds (III)are described in e.g. WO 98/47860, DT-A1-2641286 and EP-A2-0 265 824.

The present invention also relates to certain compounds which are novel.These compounds have the formula (II), where R4 is an alkyl groupcontaining 8-22, preferably 8-18, carbon atoms, n=2−7, m is 3 and eachR2 and R3 independently of each other is an alkyl group with 1-5,preferably 1-3, carbon atoms, or the formula (II), where R4 is an alkylgroup containing 8-22, preferably 8-18, carbon atoms, n=2−7, m is 2, oneof the groups R2 and R3 is —CH₂CH₂OH or —CH₂CH(CH₃)OH and the othergroup is an alkyl group with 1-5, preferably 1-3, carbon atoms,—CH₂CH₂OH, or —CH₂CH(OH₃)OH or the formula (III), where R5 isCH₃(CH₂)₃CH(CH₂CH₃)—.

The amino compounds of the present invention could be added as adjuvantsto both liquid, such as aqueous, and solid agricultural compositionscontaining pesticides, such as herbicides, acaricides, fungicides andinsecticides, as well as plant growth regulators and fertilizers. Theliquid composition could be in the form of a solution, a microemulsion,an emulsion or a suspension. Typical examples of herbicides aredifferent amine salts of glyphosate, such as the isopropylamine salt,the dimethylamine salt and the ethylenediamine salts; other salts ofglyphosate, such as the sesquisodium salt and the trimethylsulphoniumsalt; glufosinate, salts of 2,4-dichlorophenoxyacetic acid, salts of4-chloro-2-methylphenoxyacetic acid, bialaphos, dicamba, diphenylethers,imidazolinones and sulphonyl ureas. The amino compounds of the presentinvention are excellent adjuvants for the water soluble herbicides, e.g.the widely used herbicide glyphosate(glyphosate=N-(phosphonomethyl)-glycine), and the salts thereof.Suitable examples of fungicides are e.g. azoxystrobin, epoxiconazole,kcresoximmethyl and propiconazole.

Other examples of formulations where the amino compounds may be used asadjuvants are micronutrient solutions containing one or severalmicronutrients, such as iron, manganese, copper, zinc, boron andmolybdenum. The micronutrients may be complexed to e.g.aminocarboxylates, such as EDTA, DTPA, HEDTA, EDDHMA and EDDHA. Inaddition to micronutrients and chelating agents, the formulations mayalso contain macronutrients, such as nitrogen, phosphorus, potassium,magnesium and sulphur, and pesticides may also be included. Theseabove-mentioned formulations are particularly suitable for foliarapplications.

The formulations according to the invention may also contain otheradditives, such as other surfactants, hydrotropes and preservatives;additives to further enhance pesticidal activity, such as ammoniumsulphate; solvents, corrosion inhibitors, thickeners, sequesteringagents, anti-freeze agents, anti-foam agents, anti-gelling agents anddyes.

The compositions could also contain viscosity reducing agents such asglycerol, ethylene glycol, propylene glycol and low molecular weightpolyethylene or polypropylene glycols.

The compositions could be concentrates as well as diluted, “ready touse”, solutions. The concentrations may vary within wide limits, and apesticide formulation could contain 0.01-99.9% by weight of a pesticide,0-40% by weight of ammonium sulphate and an amount of 0.01-70% by weightof an amino compound according to the invention. A suitable herbicide isglyphosate, or a salt thereof, which is preferably present in an amountof 0.02-70% by weight. An adjuvant according to the present inventioncan also advantageously be used in combination with solid agrochemicalsubstances such as strobilurin analogues

wherein R6 is an aromatic or heteroaromatic substituted or unsubstitutedgroup, R7 is H or C₁-C₁₀ alkyl, A is CH or N and B is O or NH (e.g.azoxystrobin) and sulphonyl ureas to form granules or dispersions. Thestability of the dispersions may be further enhanced by the addition ofother conventional surfactants, such as nonionics, e.g. ethoxylatedfatty alcohols or amines, or alkyl glycosides containing more than 10carbon atoms in the alkyl chain. As a concentrate, the concentrationsare normally in the range of 4-70% for the pesticide, 2-50% for theadjuvants and 0-40% of ammonium sulphate, whereas for the ready-to-usesolutions the corresponding ranges are 0.01-4%, 0.01-8% and 0-40%. Thecomponents could all be mixed in the concentrate or be tank-mixed justbefore spraying the solution.

A fertilizer formulation could contain 0.0001-99.9%, preferably0.001-99.9%, by weight of a fertilizer and an amount of 0.0001-70%,preferably 0.001-70%, by weight of an amino compound according to theinvention. In a ready-to-use formulation the concentration ofmicronutrients are usually in the lower area of the range.

The following examples are illustrative of the invention and are not tobe construed as a limitation of the scope.

EXAMPLE 1

Biodegradability tests were performed with the “closed bottle test” asdescribed in OECD Test 301D. A number of amino adjuvant compoundsaccording to the invention were compared with a diester amino compoundand a monoamide compound between coco fatty acid and ethylenediaminethat had been ethoxylated with 2 moles of EO. The biodegradabilityvalues obtained after 28 days for the above-mentioned compounds aredisplayed in Table 1.

TABLE 1 Biodegradability values obtained by the OECD Test 301D.Biodegradability Compound (%) Cocoamide of N,N-bishydroxyethyl- 671,3-propylenediamine Monoester between 75 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamineMonoester between 75 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 82polyethyleneglycol (2.5 EO)- monococo ether monocarboxymethyl ether andtriethanolamine Ester between 67 polyethyleneglycol (4.5 EO)- monococoether monocarboxymethyl ether and 3-dimethylamino-1- propanol Diesterbetween 21 polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethylether and N-methyldiethanolamine (Comparative example) Monococoamide ofethylenediamine 44 ethoxylated with 2 moles of EO (Comparative example)

From these results it is evident that the amino compound adjuvants ofthe present invention exhibit a better biodegradability than thetwo-chained esteramine and the aminoamide derived from ethylenediaminethat were used as references.

EXAMPLE 2

The herbicidal effects of formulations containing the herbicideglyphosate and amino compounds according to the present invention wereinvestigated in greenhouse tests. For comparison, formulationscontaining a diester amino compound were included in the investigation.

Roundup® (a commercially available herbicidal standard formulation fromMonsanto), which contains the isopropylamine salt of glyphosate and anethoxylated fatty amine, was also included as a reference. In Roundup®the weight ratio adjuvant/glyphosate is 1:2.

The weeds used were glasshouse grown Elymus repens, Brassica napus andLolium rigidum. The treatments for Elymus repens and Brassica napus weresprayed at three dose rates; 0.15, 0.25 and 0.75 kg a.e./ha referring toglyphosate, and for Lolium rigidum the doses were 0.08, 0.15 and 0.25 kga.e./ha referring to glyphosate. The recommended dose rate forglyphosate is 1.08 kg a.e./ha. There were three replicates of eachtreatment.

The aqueous herbicide formulations were sprayed on the plants by using alaboratory track sprayer fitted with an 80015E flat fan nozzle, at aspray pressure of 210 kPA delivering 202 litres/ha.

The following formulation recipes were used for the greenhouse testsdisplayed in Tables 3-8. In some formulations also hexyl or 2-ethylhexylglucoside was added, and in those cases the amount of adjuvant stated inthe recipes below also includes the amount of glucoside. Allformulations were diluted with water before spraying. The concentrationsof the diluted solutions are displayed in Table 1 and 2 further below.

Formulation (Concentrated, Glyphosate:Adjuvant 2:1)

Glyphosate isopropyl- 13.8% w/w a.e. amine salt Amino compound adjuvant6.9% w/w Water balance

The formulation was clear and stable.

Formulation (High-Concentrated, Glyphosate:Adjuvant-5:1)

Glyphosate isopropyl- 40.7% w/w a.e. amine salt Amino compound adjuvant8.3% w/w Water balance

The formulation was clear and stable.

Formulation (High-Concentrated, Glyphosate:Adjuvant 2:1)

Glyphosate isopropyl- 30.5% w/w a.e. amine salt Amino compound adjuvant15.2% w/w Water balance

The formulation was clear and stable.

The diluted solutions that were sprayed had the concentrations displayedin the tables below.

TABLE 1 Ratio glyphosate/adjuvant¹ 2:1 Dose rate Concentration ofglyphosate Concentration of (kg/ha) acid equivalents (%) adjuvant¹ (%)0.75 0.37 0.18 0.25 0.12 0.06 0.15 0.07 0.04 0.08 0.04 0.02 ¹oradjuvant + alkyl glucoside whenever applicable.

TABLE 2 Ratio glyphosate/adjuvant² ca 5:1 Dose rate Concentration ofglyphosate Concentration of (kg/ha) acid equivalents (%) adjuvant² (%)0.75 0.37 0.075 0.25 0.12 0.025 0.15 0.07 0.014 0.08 0.04 0.008 ²oradjuvant + alkyl glucoside whenever applicable.

The experiments were assessed according to the amount of green lifegrowth and regrowth 5 weeks after spraying for Elymus repens and 4 weeksafter spraying for Brassica napus and Lolium rigidum. A score of 0-100%was used, where 100% is a totally dead plant, and for example a 50%reduction in the amount of green growth present was scored by acomparison to the best untreated plant, the latter scoring 0%.

TABLE 3 Greenhouse test with Elymus repens. The dose rates are referringto the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.15 13 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 75 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 97 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.15 8 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 65 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 95 5:1 ethyl-1,3-propylenediamine 80%Cocoamide of N,N-bis- 0.15 17 2:1 hydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 80% Cocoamide of N,N-bis- 0.25 80 2:1hydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80% Cocoamideof N,N-bis- 0.75 97 2:1 hydroxyethyl-1,3- propylenediamine + 20% hexylglucoside 50% Cocoamide of N,N-bis- 0.15 13 2:1 hydroxyethyl-1,3-propylenediamine + 50% 2-ethylhexyl glucoside 50% Cocoamide of N,N-bis-0.25 72 2:1 hydroxyethyl-1,3- propylenediamine + 50% 2-ethylhexylglucoside 50% Cocoamide of N,N-bis- 0.75 98 2:1 hydroxyethyl-1,3-propylenediamine + 50% 2-ethylhexyl glucoside 80% Cocoamide of N,N-bis-0.15 13 5:1 hydroxyethyl-1,3- propylenediamine + 20% 2-ethylhexylglucoside 80% Cocoamide of N,N-bis- 0.25 57 5:1 hydroxyethyl-1,3-propylenediamine + 20% 2-ethylhexyl glucoside 80% Cocoamide of N,N-bis-0.75 93 5:1 hydroxyethyl-1,3- propylenediamine + 20% 2-ethylhexylglucoside 80% Cocoamide of N,N-bis- 0.15 8 5:1 hydroxyethyl-1,3-propylenediamine + 20% hexyl glucoside 80% Cocoamide of N,N-bis- 0.25 505:1 hydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80%Cocoamide of N,N-bis- 0.75 95 5:1 hydroxyethyl-1,3- propylenediamine +20% hexyl glucoside Cocoamide of N,N-bishydroxy- 0.15 27 5:1ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) Cocoamide of N,N-bishydroxy- 0.25 67 5:1ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) Cocoamide of N,N-bishydroxy- 0.75 95 5:1ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) 50% 2-Ethylhexylamide of 0.15 10 2:1N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%2-Ethylhexylamide of 0.25 38 2:1 N,N-bishydroxyethyl-1,3-propylenediamine + 50% hexyl glucoside 50% 2-Ethylhexylamide of 0.75 922:1 N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.15 13 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside 50% Oleylamide of N,N- 0.25 73 2:1bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.75 92 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside Ester between 0.15 17 2:1 polyethyleneglycol (4.5EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 73 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.75 93 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.15 5 2:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.25 67 2:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.75 92 2:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Ester between 0.15 10 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 58 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.75 92 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.15 3 5:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.25 40 5:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.75 92 5:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Roundup 0.15 15 2:1 Roundup 0.25 72 2:1Roundup 0.75 98 2:1

TABLE 4 Greenhouse test with Brassica napus. The dose rates arereferring to the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.15 40 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 70 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 98 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.15 8 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 73 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 87 5:1 ethyl-1,3-propylenediamine 80%Cocoamide of N,N-bis- 0.15 25 2:1 hydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 80% Cocoamide of N,N- 0.25 68 2:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80%Cocoamide of N,N- 0.75 93 2:1 bishydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 50% Cocoamide of N,N- 0.15 37 2:1bishydroxyethyl-1,3- propylenediamine + 50% 2-ethylhexyl glucoside 50%Cocoamide of N,N- 0.25 68 2:1 bishydroxyethyl-1,3- propylenediamine +50% 2-ethylhexyl glucoside 50% Cocoamide of N,N- 0.75 93 2:1bishydroxyethyl-1,3- propylenediamine + 50% 2-ethylhexyl glucoside 80%Cocoamide of N,N- 0.15 35 5:1 bishydroxyethyl-1,3- propylenediamine +20% 2-ethylhexyl glucoside 80% Cocoamide of N,N- 0.25 57 5:1bishydroxyethyl-1,3- propylenediamine + 20% 2-ethylhexyl glucoside 80%Cocoamide of N,N- 0.75 95 5:1 bishydroxyethyl-1,3- propylenediamine +20% 2-ethylhexyl glucoside 80% Cocoamide of N,N- 0.15 17 5:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80%Cocoamide of N,N- 0.25 67 5:1 bishydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 80% Cocoamide of N,N- 0.75 93 5:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside Cocoamide ofN,N-bishydroxy- 0.15 60 5:1 ethyl-1,3-propylenediamine + ammoniumsulphate (3% w/w of the concentrate) Cocoamide of N,N-bishydroxy- 0.2572 5:1 ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) Cocoamide of N,N-bishydroxy- 0.75 93 5:1ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) 50% 2-Ethylhexylamide of 0.15 20 2:1N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%2-Ethylhexylamide of 0.25 52 2:1 N,N-bishydroxyethyl-1,3-propylenediamine + 50% hexyl glucoside 50% 2-Ethylhexylamide of 0.75 922:1 N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.15 15 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside 50% Oleylamide of N,N- 0.25 62 2:1bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.75 83 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside Ester between 0.15 17 2:1 polyethyleneglycol (4.5EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 73 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.75 92 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.15 17 2:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.25 63 2:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.75 93 2:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Ester between 0.15 15 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 62 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.75 97 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.15 28 5:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.25 57 5:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.75 92 5:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Hexyl glucoside 0.75 57 2:1 (Reference)2-ethylhexyl glucoside 0.75 63 2:1 (Reference) Roundup 0.15 27 2:1Roundup 0.25 67 2:1 Roundup 0.75 95 2:1

TABLE 5 Greenhouse test with Lolium rigidum. The dose rates arereferring to the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.08 57 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.15 78 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 97 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.08 23 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.15 72 5:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 88 5:1 ethyl-1,3-propylenediamine 80%Cocoamide of N,N- 0.08 18 2:1 bishydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 80% Cocoamide of N,N- 0.15 60 2:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80%Cocoamide of N,N- 0.25 88 2:1 bishydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 50% Cocoamide of N,N- 0.08 17 2:1bishydroxyethyl-1,3- propylenediamine + 50% 2-ethylhexyl glucoside 50%Cocoamide of N,N- 0.15 62 2:1 bishydroxyethyl-1,3- propylenediamine +50% 2-ethylhexyl glucoside 50% Cocoamide of N,N- 0.25 97 2:1bishydroxyethyl-1,3- propylenediamine + 50% 2-ethylhexyl glucoside 80%Cocoamide of N,N- 0.08 60 5:1 bishydroxyethyl-1,3- propylenediamine +20% 2-ethylhexyl glucoside 80% Cocoamide of N,N- 0.15 62 5:1bishydroxyethyl-1,3- propylenediamine + 20% 2-ethylhexyl glucoside 80%Cocoamide of N,N- 0.25 87 5:1 bishydroxyethyl-1,3- propylenediamine +20% 2-ethylhexyl glucoside 80% Cocoamide of N,N- 0.08 52 5:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside 80%Cocoamide of N,N- 0.15 47 5:1 bishydroxyethyl-1,3- propylenediamine +20% hexyl glucoside 80% Cocoamide of N,N- 0.25 80 5:1bishydroxyethyl-1,3- propylenediamine + 20% hexyl glucoside Cocoamide ofN,N-bishydroxy- 0.08 15 5:1 ethyl-1,3-propylenediamine + ammoniumsulphate (3% w/w of the concentrate) Cocoamide of N,N-bishydroxy- 0.1553 5:1 ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) Cocoamide of N,N-bishydroxy- 0.25 65 5:1ethyl-1,3-propylenediamine + ammonium sulphate (3% w/w of theconcentrate) 50% 2-Ethylhexylamide of 0.08 43 2:1N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%2-Ethylhexylamide of 0.15 50 2:1 N,N-bishydroxyethyl-1,3-propylenediamine + 50% hexyl glucoside 50% 2-Ethylhexylamide of 0.25 882:1 N,N-bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.08 13 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside 50% Oleylamide of N,N- 0.15 35 2:1bishydroxyethyl-1,3- propylenediamine + 50% hexyl glucoside 50%Oleylamide of N,N- 0.25 70 2:1 bishydroxyethyl-1,3- propylenediamine +50% hexyl glucoside Ester between 0.08 12 2:1 polyethyleneglycol (4.5EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.15 48 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 87 2:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.08 27 2:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.15 57 2:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.25 75 2:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Ester between 0.08 48 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.15 80 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol Ester between 0.25 93 5:1 polyethyleneglycol(4.5 EO)- monococo ether monocarboxymethyl ether and3-dimethylamino-1-propanol 50% Diester between 0.08 8 5:1polyethyleneglycol (4.5 EO)- monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside (Reference) 50% Diesterbetween 0.15 33 5:1 polyethyleneglycol (4.5 EO)- monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucoside(Reference) 50% Diester between 0.25 70 5:1 polyethyleneglycol (4.5 EO)-monococo ether monocarboxymethyl ether and N-methyldiethanolamine + 50%hexyl glucoside (Reference) Roundup 0.08 37 2:1 Roundup 0.15 45 2:1Roundup 0.25 88 2:1

As is shown from the tables, the amino compound adjuvants according tothe present invention are comparable or more efficient adjuvants for theherbicide than the amino compound containing two alkyl chains. Theformulations based on the amino compound adjuvants also exhibitcomparable or better herbicidal efficacy than the Roundup formulation.

EXAMPLE 3

Greenhouse tests were performed as described in example 2, with theexception that the amount of green life and regrowth was assessed 7weeks after spraying for Elymus repens. Roundup was included as areference.

TABLE 6 Greenhouse test with Elymus repens. The dose rates are referringto the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.15 33 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 47 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 100 2:1 ethyl-1,3-propylenediamineMonoester between 0.15 37 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine Monoester between0.25 83 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine Monoester between 0.75 98 2:1polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine Monoester between 0.15 28 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.25 75 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.75 1002:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl etherand triethanolamine Monoester between 0.15 35 2:1 polyethyleneglycol(2.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.25 43 2:1 polyethyleneglycol (2.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.75 1002:1 polyethyleneglycol (2.5 EO) monococo ether monocarboxymethyl etherand triethanolamine 50% Monoester between 0.15 65 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside 50% Monoester between 0.2577 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine + 50% hexyl glucoside 50% Monoesterbetween 0.75 100 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucosideRoundup 0.15 15 2:1 Roundup 0.25 27 2:1 Roundup 0.75 97 2:1

TABLE 7 Greenhouse test with Brassica napus. The dose rates arereferring to the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.15 45 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 52 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.75 90 2:1 ethyl-1,3-propylenediamineMonoester between 0.15 55 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine Monoester between0.25 70 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine Monoester between 0.75 92 2:1polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine Monoester between 0.15 58 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.25 75 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.75 922:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl etherand triethanolamine Monoester between 0.15 42 2:1 polyethyleneglycol(2.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.25 52 2:1 polyethyleneglycol (2.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.75 902:1 polyethyleneglycol (2.5 EO) monococo ether monocarboxymethyl etherand triethanolamine 50% Monoester between 0.15 67 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside 50% Monoester between 0.2557 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine + 50% hexyl glucoside 50% Monoesterbetween 0.75 95 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucosideRoundup 0.15 45 2:1 Roundup 0.25 65 2:1 Roundup 0.75 87 2:1

TABLE 8 Greenhouse test with Lolium rigidum. The dose rates arereferring to the amount of glyphosate, the amount of adjuvant oradjuvant/glucoside mixture being half or one fifth of that amount.Glyphosate/ Dose rate Effect adjuvant Adjuvant (kg/ha) (%) ratioCocoamide of N,N-bishydroxy- 0.08 40 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.15 58 2:1 ethyl-1,3-propylenediamineCocoamide of N,N-bishydroxy- 0.25 93 2:1 ethyl-1,3-propylenediamineMonoester between 0.08 50 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine Monoester between0.15 77 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine Monoester between 0.25 95 2:1polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine Monoester between 0.08 52 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.15 72 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.25 962:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethyl etherand triethanolamine Monoester between 0.08 48 2:1 polyethyleneglycol(2.5 EO) monococo ether monocarboxymethyl ether and triethanolamineMonoester between 0.15 68 2:1 polyethyleneglycol (2.5 EO) monococo ethermonocarboxymethyl ether and triethanolamine Monoester between 0.25 882:1 polyethyleneglycol (2.5 EO) monococo ether monocarboxymethyl etherand triethanolamine 50% Monoester between 0.08 47 2:1 polyethyleneglycol(4.5 EO) monococo ether monocarboxymethyl ether andN-methyldiethanolamine + 50% hexyl glucoside 50% Monoester between 0.1583 2:1 polyethyleneglycol (4.5 EO) monococo ether monocarboxymethylether and N-methyldiethanolamine + 50% hexyl glucoside 50% Monoesterbetween 0.25 90 2:1 polyethyleneglycol (4.5 EO) monococo ethermonocarboxymethyl ether and N-methyldiethanolamine + 50% hexyl glucosideRoundup 0.08 47 2:1 Roundup 0.15 60 2:1 Roundup 0.25 72 2:1

EXAMPLE 4

The fungicidal effect of a formulation containing the fungicide Amistar(azoxystrobin) and the cocoamide ofN,N-bishydroxyethyl-1,3-propylenediamine was compared to the fungicidaleffect of Amistar alone.

A semi-field trial was performed using spring wheat that wasartificially inoculated with Stagonospora nodorum. The fungicideformulation was applied 4 days after inoculation with a cabin sprayerwith flat fan nozzles under a pressure of 4.2 bar, delivering 230 l/ha.Disease assessments were carried out 29 days after inoculation. Attackof Stagonospora nodorum was assessed as percent coverage of the secondgreen leaves. Percent control on the fungicide-treated plants wascalculated using the formula 100−100×A/B, where A is the attack ontreated plants and B is the attack on untreated plants. At a dosage of0.0625 l/ha of Amistar and 1.5 l/ha of the cocoamide ofN,N-bishydroxyethyl-1,3-propylenediamine, there was an improvement inthe fungicidal effect as compared to when Amistar was used alone. WithAmistar alone 54% control of Stagonospora nodorum was obtained whereasfor the addition of Amistar and the above-mentioned amidoamine 69.5%control was obtained. No phytotoxicity was seen after adding theadjuvant to Amistar.

What is claimed is:
 1. An agrochemical adjuvant of the formula:

where R1 is an aliphatic group containing 7-22 carbon atoms; EO is anethyleneoxy group; Y is O or NH; R2 and R3 is independently —CH₂CH₂OH,—CH₂CH(CH₃)OH or an alkyl group with 1-5 carbon atoms; n is a numberbetween 0-10; x is a number 0-1 provided that when Y is O, then x is 1,and when Y is NH, then x is 0; and m is a number 2-6, provided that whenY is NH, then m is 3-6; or an adduct obtained by reacting one mole ofthe compound with 1-5 moles of an alkylene oxide having 2-3 carbonatoms.
 2. The adjuvant of claim 1 having the formula:

where R4 is an alkyl group containing 8-22 carbon atoms, n is 2-7, m isa number 2-3 and R2 a R3 is independently —CH₂CH₂OH, —CH₂CH(CH₃)OH or analkyl group with 1-5 carbon atoms.
 3. The adjuvant of claim 1 having theformula:

where R5 is an alkyl group containing 7-21 carbon atoms.
 4. Anagrochemical composition which comprises at least one agrochemicalselected from the group consisting of a pesticide, a fertilizer andmixtures thereof, and which additionally comprises the adjuvant ofclaim
 1. 5. The composition of claim 4 wherein said adjuvant is of theformula where R4 is an alkyl group containing 8-22 carbon atoms, n is2-7, m is a number 2-3 and R2 and:

R3 is independently —CH₂CH₂OH, —CH₂CH(CH₃)OH or an alkyl group with 1-5carbon atoms.
 6. The composition of claim 4 wherein said adjuvant is ofthe formula:

where R5 is an alkyl group containing 7-21 carbon atoms.
 7. Thecomposition of claim 4 which additionally comprises an alkyl glycosideROG_(p), where R is an alkyl group containing 6-10 carbon atoms, G is amonosaccharide residue and p is a number between 1-5.
 8. The compositionof claim 4 in solid granular form.
 9. The composition of claim 4 in theform of a liquid solution, an emulsion or a suspension.
 10. Anagrochemical formulation which comprises 0.0 1-99.9% by weight of anagrochemical, 0-40% by weight of ammonium sulphate and 0.01-70% byweight of an adjuvant, wherein said adjuvant is selected from the groupconsisting of the adjuvant of claim 1, the adjuvant of formula (II):

where R4 is an alkyl group containing 8-22 carbon atoms, n is 2-7, m isa number 2-3 and R2 an R3 is independently —CH₂CH₂OH, —CH₂CH(CH₃)OH oran alkyl group with 1-5 carbon atoms; the adjuvant of formula (III):

where R5 is an alkyl group containing 7-21 carbon atoms, and mixturesthereof.
 11. The formulation of claim 10 wherein the agrochemical is apesticide and said pesticide is a strobilurin analogue or a sulphonylurea.
 12. The formulation of claim 10 wherein said agrochemical is aherbicide and said herbicide herbicide is glyphosate(=N-(phosphonomethyl)glycine) or a salt thereof.
 13. A fertilizerformulation which comprises 0.0001-99.9% by weight of a fertilizer and0.0001-70% by weight of an adjuvant, wherein said adjuvant is selectedfrom the group consisting of the adjuvant of claim 1, the adjuvant offormula (II);

where R4 is an alkyl group containing 8-22 carbon atoms, n is 2-7, m isa number 2-3 and R2 an R3 is independently —CH₂CH₂OH, —CH₂CH(CH₃)OH oran alkyl group with 1-5 carbon atoms; the adj uvant of formula (III):

where R5 is an alkyl group containing 7-21 carbon atoms, and mixturesthereof.
 14. The adjuvant of claim 3, where R5 is CH₃(CH₂)₃CH(CH₂CH₃)—.15. The adjuvant of claim 2, where R4 is an alkyl group containing 8-2carbon atoms, n=2-7, m is 3 and each R2 and R3 independently of eachother is an alkyl group with 1-5 carbon atoms.
 16. The adjuvant of claim2, where R4 is an alkyl group containing 8-22 carbon atoms, n=2-7, m is2, one of the groups R2 and R3 is —CH₂CH₂OH or —CH₂CH(CH₃)OH and theother group is an alkyl group with 1-5 carbon atoms, —CH₂CH₂OH or—CH₂CH(CH₃)OH.